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    Chemistry

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    Also known as: 21256-18-8, Daypro, 3-(4,5-diphenyl-1,3-oxazol-2-yl)propanoic acid, Alvo, 3-(4,5-diphenyloxazol-2-yl)propanoic acid, Oxaprozine
    Molecular Formula
    C18H15NO3
    Molecular Weight
    293.3  g/mol
    InChI Key
    OFPXSFXSNFPTHF-UHFFFAOYSA-N
    FDA UNII
    MHJ80W9LRB
    Oxaprozin
    An oxazole-propionic acid derivative, cyclooxygenase inhibitor, and non-steroidal anti-inflammatory drug that is used in the treatment of pain and inflammation associated with of OSTEOARTHRITIS; RHEUMATOID ARTHRITIS; and ARTHRITIS, JUVENILE.
    Oxaprozin is a Nonsteroidal Anti-inflammatory Drug. The mechanism of action of oxaprozin is as a Cyclooxygenase Inhibitor.
    1 2D Structure

    Oxaprozin

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    3-(4,5-diphenyl-1,3-oxazol-2-yl)propanoic acid
    2.1.2 InChI
    InChI=1S/C18H15NO3/c20-16(21)12-11-15-19-17(13-7-3-1-4-8-13)18(22-15)14-9-5-2-6-10-14/h1-10H,11-12H2,(H,20,21)
    2.1.3 InChI Key
    OFPXSFXSNFPTHF-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=CC=C(C=C1)C2=C(OC(=N2)CCC(=O)O)C3=CC=CC=C3
    2.2 Other Identifiers
    2.2.1 UNII
    MHJ80W9LRB
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4,5 Diphenyl 2 Oxazolepropionic Acid

    2. 4,5-diphenyl-2-oxazolepropionic Acid

    3. Apo Oxaprozin

    4. Apo-oxaprozin

    5. Danoprox

    6. Daypro

    7. Dayrun

    8. Rhoxal Oxaprozin

    9. Rhoxal-oxaprozin

    10. Wy 21,743

    11. Wy-21,743

    2.3.2 Depositor-Supplied Synonyms

    1. 21256-18-8

    2. Daypro

    3. 3-(4,5-diphenyl-1,3-oxazol-2-yl)propanoic Acid

    4. Alvo

    5. 3-(4,5-diphenyloxazol-2-yl)propanoic Acid

    6. Oxaprozine

    7. Oxaprozinum

    8. Deflam

    9. Wy-21,743

    10. Oxaprozine [inn-french]

    11. Oxaprozinum [inn-latin]

    12. Wy-21743

    13. Oxaprozina [inn-spanish]

    14. Oxaprozina

    15. 4,5-diphenyl-2-oxazolepropanoic Acid

    16. 4,5-diphenyl-2-oxazolepropionic Acid

    17. 2-oxazolepropanoic Acid, 4,5-diphenyl-

    18. Duraprox

    19. Oxaprozinum;wy21743

    20. Wy 21743

    21. Mfcd00215977

    22. Nsc310839

    23. Nsc-310839

    24. 3-(4,5-diphenyl-2-oxazolyl)propenoic Acid

    25. 3-(diphenyl-1,3-oxazol-2-yl)propanoic Acid

    26. Beta-(4,5-diphenyloxazol-2-yl)propionic Acid

    27. Mhj80w9lrb

    28. Nsc 310839

    29. Chembl1071

    30. Chebi:7822

    31. Voir

    32. 2-oxazolepropionic Acid, 4,5-diphenyl-

    33. .beta.-(4,5-diphenyloxazol-2-yl)propionic Acid

    34. Danoprox

    35. Dayrun

    36. 3-(4,5-diphenyl-2-oxazolyl)propanoic Acid

    37. Cas-21256-18-8

    38. Dsstox_cid_25118

    39. Dsstox_rid_80684

    40. Dsstox_gsid_45118

    41. Actirin

    42. Xopane

    43. Smr000058286

    44. Daypro (tn)

    45. Sr-01000076053

    46. Oxaprosin

    47. Durapro

    48. Duraprost

    49. Oxaprozi

    50. Oxapro

    51. Walix

    52. Oxaprozin, Solid

    53. Oxaprozin,(s)

    54. Oxaprozin- Bio-x

    55. Einecs 244-296-1

    56. Nci310839

    57. 4, 5-diphenyl-2-oxazolepropionic Acid

    58. Brn 1083168

    59. Oxaprozin [inn]

    60. Oxaprozin [jan]

    61. Oxaprozin [mi]

    62. Oxaprozin [hsdb]

    63. Oxaprozin [usan]

    64. Maybridge1_008800

    65. Prestwick0_001060

    66. Prestwick1_001060

    67. Prestwick2_001060

    68. Prestwick3_001060

    69. Spectrum2_001696

    70. Spectrum3_001078

    71. Spectrum4_001231

    72. Unii-mhj80w9lrb

    73. Lopac-o-9637

    74. Oxaprozin [vandf]

    75. Oxaprozin [mart.]

    76. O 9637

    77. Oxaprozin [usp-rs]

    78. Oxaprozin [who-dd]

    79. Schembl3286

    80. Ncistruc1_000799

    81. Ncistruc2_000787

    82. Bidd:pxr0149

    83. Lopac0_000944

    84. Oprea1_509470

    85. Bspbio_001020

    86. Bspbio_002696

    87. Kbiogr_001722

    88. Mls000759535

    89. Mls001424072

    90. Bidd:gt0438

    91. Spectrum1505267

    92. Spbio_001652

    93. Spbio_002940

    94. Oxaprozin (jp17/usp/inn)

    95. Bpbio1_001122

    96. Gtpl7252

    97. Oxaprozin [orange Book]

    98. Dtxsid1045118

    99. Hms566h22

    100. Hsdb 7586

    101. Kbio3_001916

    102. Oxaprozin [usp Monograph]

    103. Hms1571c22

    104. Hms1922p17

    105. Hms2051l15

    106. Hms2093o08

    107. Hms2098c22

    108. Hms3262n10

    109. Hms3393l15

    110. Hms3652h17

    111. Hms3715c22

    112. Hms3885l11

    113. Pharmakon1600-01505267

    114. Wy21743

    115. Amy32551

    116. Bcp28431

    117. Hy-b0808

    118. Tox21_110059

    119. Tox21_500944

    120. 2-oxazolepropanoic Acid,5-diphenyl-

    121. 2-oxazolepropionic Acid,5-diphenyl-

    122. Bdbm50002861

    123. Ccg-36508

    124. Ncgc00014711

    125. Nsc758949

    126. S4230

    127. Zinc49643479

    128. 4,5-diphenyloxazole-2-propanoic Acid

    129. Oxaprozin 100 Microg/ml In Methanol

    130. 4,5-diphenyloxazole-2-propionic Acid

    131. Akos000206807

    132. Oxaprozin [usan:usp:inn:ban:jan]

    133. Tox21_110059_1

    134. Cs-7975

    135. Db00991

    136. Ks-5196

    137. Lp00944

    138. Nc00214

    139. Nsc-758949

    140. Sdccgsbi-0050918.p004

    141. Ncgc00014711-01

    142. Ncgc00014711-02

    143. Ncgc00014711-03

    144. Ncgc00014711-04

    145. Ncgc00014711-05

    146. Ncgc00014711-06

    147. Ncgc00014711-07

    148. Ncgc00014711-08

    149. Ncgc00014711-09

    150. Ncgc00014711-10

    151. Ncgc00014711-11

    152. Ncgc00014711-14

    153. Ncgc00014711-15

    154. Ncgc00094249-01

    155. Ncgc00094249-02

    156. Ncgc00094249-03

    157. Ncgc00094249-04

    158. Ncgc00094249-05

    159. Ncgc00094249-06

    160. Ncgc00094249-07

    161. Ncgc00261629-01

    162. Oxaprozin 100 Microg/ml In Acetonitrile

    163. Ac-26512

    164. Bo164184

    165. Nci60_002681

    166. Sy050819

    167. Sbi-0050918.p002

    168. 3-(4,5-diphenyl-2-oxazolyl)propionic Acid

    169. Ab00514024

    170. B1804

    171. Eu-0100944

    172. Ft-0638104

    173. O0377

    174. Sw197319-4

    175. 3-(4, 5-diphenyl-2-oxazolyl)propenoic Acid

    176. En300-25629

    177. 3-(4,5-diphenyl-oxazol-2-yl)-propionic Acid

    178. C07356

    179. D00463

    180. Ab00514024_08

    181. Ab00514024_09

    182. 256o188

    183. A815225

    184. 1-aminocyclobutane-cis-1,3-dicarboxylicacid

    185. J-013955

    186. Q1749609

    187. Sr-01000076053-1

    188. Sr-01000076053-3

    189. Sr-01000076053-7

    190. Sr-01000076053-9

    191. 3-(4,5-diphenyl-1,3-oxazol-2-yl)propanoic Acid #

    192. Brd-k25394294-001-05-7

    193. Brd-k25394294-001-08-1

    194. Z217102860

    195. Oxaprozin, United States Pharmacopeia (usp) Reference Standard

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 293.3 g/mol
    Molecular Formula C18H15NO3
    XLogP34.2
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count5
    Exact Mass293.10519334 g/mol
    Monoisotopic Mass293.10519334 g/mol
    Topological Polar Surface Area63.3 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity361
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameDaypro
    PubMed HealthOxaprozin (By mouth)
    Drug ClassesAnalgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
    Drug LabelDAYPRO (oxaprozin) is a nonsteroidal anti-inflammatory drug (NSAID), chemically designated as 4,5-diphenyl-2-oxazole-propionic acid, and has the following chemical structure:The empirical formula for oxaprozin is C18H15NO3, and the molecular weight i...
    Active IngredientOxaprozin
    Dosage FormTablet
    RouteOral
    Strength600mg
    Market StatusPrescription
    CompanyGd Searle

    2 of 4  
    Drug NameOxaprozin
    PubMed HealthOxaprozin (By mouth)
    Drug ClassesAnalgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
    Drug LabelOxaprozin, USP is a nonsteroidal anti-inflammatory drug (NSAID), chemically designated as 4,5-diphenyl-2-oxazole-propionic acid, and has the following chemical structure:The empirical formula for oxaprozin, USP is C18H15NO3, and the molecular weight...
    Active IngredientOxaprozin
    Dosage FormTablet
    RouteOral
    Strength600mg
    Market StatusPrescription
    CompanyTeva; Apotex; Sun Pharm Inds; Sandoz; Ivax Sub Teva Pharms; Dr Reddys Labs

    3 of 4  
    Drug NameDaypro
    PubMed HealthOxaprozin (By mouth)
    Drug ClassesAnalgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
    Drug LabelDAYPRO (oxaprozin) is a nonsteroidal anti-inflammatory drug (NSAID), chemically designated as 4,5-diphenyl-2-oxazole-propionic acid, and has the following chemical structure:The empirical formula for oxaprozin is C18H15NO3, and the molecular weight i...
    Active IngredientOxaprozin
    Dosage FormTablet
    RouteOral
    Strength600mg
    Market StatusPrescription
    CompanyGd Searle

    4 of 4  
    Drug NameOxaprozin
    PubMed HealthOxaprozin (By mouth)
    Drug ClassesAnalgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
    Drug LabelOxaprozin, USP is a nonsteroidal anti-inflammatory drug (NSAID), chemically designated as 4,5-diphenyl-2-oxazole-propionic acid, and has the following chemical structure:The empirical formula for oxaprozin, USP is C18H15NO3, and the molecular weight...
    Active IngredientOxaprozin
    Dosage FormTablet
    RouteOral
    Strength600mg
    Market StatusPrescription
    CompanyTeva; Apotex; Sun Pharm Inds; Sandoz; Ivax Sub Teva Pharms; Dr Reddys Labs

    4.2 Therapeutic Uses

    Oxaprozin ... /is/ indicated for the treatment of acute or chronic rheumatoid arthritis. /Included in US product labeling/

    Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 376

    Oxaprozin ... /is/ indicated for relief of acute or chronic osteoarthritis. /Included in US product labeling/

    Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 376

    ... In this open, multicenter, randomized, controlled study, eligible patients with periarthritis of the shoulder were randomized to receive either oxaprozin 1200 mg once daily (n = 49) or diclofenac 50 mg three times daily (n = 47). The treatment period was 15 +/- 1 days. The study was planned on a hypothesis of equivalence between the two study drugs. The primary study endpoint was the change from baseline at day 15 in the patient-assessed shoulder pain score. Secondary efficacy variables included investigator-assessed shoulder function, patient-assessed quality of life on the Short-Form-36 (SF-36) Acute Health Survey and both patients' and investigators' overall assessment of efficacy. At day 15, the mean changes in shoulder pain score from baseline in the oxaprozin and diclofenac groups were -5.85 +/- SD 4.62 and -5.54 +/- SD 4.41, respectively. The difference between the two groups was not statistically significant, confirming the hypothesis of the study that oxaprozin is as effective as diclofenac. Investigator-assessed shoulder function improved in both groups but more so in the oxaprozin group (p = 0.028 at day 15). Quality of life as measured by SF-36 total score was also improved in both treatment groups, with a trend toward greater improvement in the oxaprozin group. Furthermore, a significantly more favorable effect on the SF-36 'mental health' item was observed in oxaprozin compared with diclofenac-treated patients at day 15 (p = 0.0202). As assessed by investigators, the overall efficacy of oxaprozin was superior to that for diclofenac at visit 3 (8 +/- 1 days) (p = 0.0067). Patients also assessed the overall efficacy of oxaprozin as superior to that of diclofenac at visits 3 (8 +/- 1 days) (p = 0.0235) and 4 (15 +/- 1 days) (p = 0.0272). Only six adverse events, all of which were mild or moderate in intensity and occurred in four diclofenac recipients, were observed in the study. As expected, once-daily oxaprozin proved to be as effective as diclofenac three times daily in reducing the primary efficacy variable of patient-assessed shoulder pain score in patients with periarthritis of the shoulder refractory to previous treatments with other NSAIDs. Oxaprozin was shown to be superior to diclofenac in improving shoulder function and was considered by investigators and patients to have greater overall efficacy than diclofenac. In addition, oxaprozin showed a trend toward superior results in improving patients' quality of life compared with diclofenac. A trend towards better tolerability results for oxaprozin compared with diclofenac was also noted.

    PMID:15324531 Heller B, Tarricone R; Curr Med Res Opin 20 (8): 1279-90 (2004)

    /EXPL THER/: The effects of eye drops containing a propionic acid derivative (oxaprozin) at 0.1% concentration on ocular inflammation produced by sodium arachidonate in the rabbit's eye were evaluated. Furthermore, the aqueous bioavailability of the drug formulation in the uninflamed and inflamed eyes was evaluated. Oxaprozin eye drops significantly reduced the signs of ocular inflammation elicited by sodium arachidonate on conjunctiva and iris. Oxaprozin treatment significantly reduced the levels of polymorphonuclear leukocytes and protein concentration in aqueous samples obtained from the eyes treated with arachidonate. Present data suggest, for the first time, that oxaprozin may be employed topically to prevent ocular reactions where the arachidonic acid cascade is activated.

    PMID:11858617 Bucolo C, Maltese A; J Ocul Pharmacol Ther 18 (1): 75-81 (2002)

    4.3 Drug Warning

    Clinical trials of several COX-2 selective and nonselective NSAIDs of up to three years duration have shown an increased risk of serious cardiovascular thrombotic events, myocardial infarction, and stroke, which can be fatal. All NSAIDs, both COX-2 selective and nonselective, may have a similar risk. Patients with known cardiovascular disease or risk factors for cardiovascular disease may be at greater risk. To minimize the potential risk for an adverse cardiovascular event in patients treated with a NSAID, the lowest effective dose should be used for the shortest duration possible. Physicians and patients should remain alert for the development of such events, even in the absence of previous cardiovascular symptoms. Patients should be informed about the signs and/or symptoms of serious cardiovascular events and the steps to take if they occur. /Nonsteroidal anti-inflammatory drugs/

    Prescribing Information for Daypro (Oxaprozin); G.D. Searle LLC, Div. of Pfizer Inc, USA; (January 2007). Available from, as of February 12, 2008: https://media.pfizer.com/files/products/uspi_daypro.pdf

    NSAIDs, including Daypro, can cause serious gastrointestinal (GI) adverse events including inflammation, bleeding, ulceration, and perforation of the stomach, small intestine, or large intestine, which can be fatal. These serious adverse events can occur at any time, with or without warning symptoms, in patients treated with NSAIDs. Only one in five patients, who develop a serious upper GI adverse event on NSAID therapy, is symptomatic. Upper GI ulcers, gross bleeding, or perforation caused by NSAIDs occur in approximately 1% of patients treated for 3-6 months, and in about 2-4% of patients treated for one year. These trends continue with longer duration of use, increasing the likelihood of developing a serious GI event at some time during the course of therapy. However, even short-term therapy is not without risk.

    Prescribing Information for Daypro (Oxaprozin); G.D. Searle LLC, Div. of Pfizer Inc, USA; (January 2007). Available from, as of February 12, 2008: https://media.pfizer.com/files/products/uspi_daypro.pdf

    NSAIDs should be prescribed with extreme caution in those with a prior history of ulcer disease or gastrointestinal bleeding. Patients with a prior history of peptic ulcer disease and/or gastrointestinal bleeding who use NSAIDs have a greater than 10-fold increased risk for developing a GI bleed compared to patients treated with neither of these risk factors. Other factors that increase the risk of GI bleeding in patients treated with NSAIDs include concomitant use of oral corticosteroids or anticoagulants, longer duration of NSAID therapy, smoking, use of alcohol, older age, and poor general health status. Most spontaneous reports of fatal GI events are in elderly or debilitated patients and therefore, special care should be taken in treating this population. To minimize the potential risk for an adverse GI event in patients treated with an NSAID, the lowest effective dose should be used for the shortest possible duration. Patients and physicians should remain alert for signs and symptoms of GI ulcerations and bleeding during NSAID therapy and promptly initiate additional evaluation and treatment if a serious GI event is suspected. This should include discontinuation of the NSAID until a serious GI adverse event is ruled out. For high risk patients, alternate therapies that do not involve NSAIDs should be considered. /Nonsteroidal anti-inflammatory drugs/

    Prescribing Information for Daypro (Oxaprozin); G.D. Searle LLC, Div. of Pfizer Inc, USA; (January 2007). Available from, as of February 12, 2008: https://media.pfizer.com/files/products/uspi_daypro.pdf

    As with other NSAIDs, anaphylactoid reactions may occur in patients without known prior exposure to Daypro. Daypro should not be given to patients with the aspirin triad. This symptom complex typically occurs in asthmatic patients who experience rhinitis with or without nasal polyps, or who exhibit severe, potentially fatal bronchospasm after taking aspirin or other NSAIDs

    Prescribing Information for Daypro (Oxaprozin); G.D. Searle LLC, Div. of Pfizer Inc, USA; (January 2007). Available from, as of February 12, 2008: https://media.pfizer.com/files/products/uspi_daypro.pdf

    For more Drug Warnings (Complete) data for OXAPROZIN (18 total), please visit the HSDB record page.

    4.4 Drug Indication

    Used to relieve the inflammation, swelling, stiffness, and joint pain associated with rheumatoid arthritis and osteoarthritis.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Oxaprozin is a nonsteroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic properties. Oxaprozin is used to treat rheumatoid arthritis, osteoarthritis, dysmenorrhea, and to alleviate moderate pain.

    5.2 MeSH Pharmacological Classification

    Anti-Inflammatory Agents, Non-Steroidal

    Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

    Cyclooxygenase Inhibitors

    Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes. (See all compounds classified as Cyclooxygenase Inhibitors.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    OXAPROZIN
    5.3.2 FDA UNII
    MHJ80W9LRB
    5.3.3 Pharmacological Classes
    Cyclooxygenase Inhibitors [MoA]; Nonsteroidal Anti-inflammatory Drug [EPC]; Anti-Inflammatory Agents, Non-Steroidal [CS]
    5.4 ATC Code

    M - Musculo-skeletal system

    M01 - Antiinflammatory and antirheumatic products

    M01A - Antiinflammatory and antirheumatic products, non-steroids

    M01AE - Propionic acid derivatives

    M01AE12 - Oxaprozin

    5.5 Absorption, Distribution and Excretion

    Absorption

    Oxaprozin is 95% absorbed after oral administration. Food may reduce the rate of absorption of oxaprozin, but the extent of absorption is unchanged. Antacids do not significantly affect the extent and rate of oxaprozin absorption.

    Route of Elimination

    Oxaprozin is expected to be excreted in human milk based on its physical-chemical properties; however, the amount of oxaprozin excreted in breast milk has not been evaluated. Approximately 95% of oxaprozin is metabolized by the liver. Approximately 5% of the oxaprozin dose is excreted unchanged in the urine. Sixty-five percent (65%) of the dose is excreted in the urine and 35% in the feces as metabolite. Biliary excretion of unchanged oxaprozin is a minor pathway. Several oxaprozin metabolites have been identified in human urine or feces.

    Volume of Distribution

    11 to 17 L/70 kg

    In dose proportionality studies utilizing 600, 1200 and 1800 mg doses, the pharmacokinetics of oxaprozin in healthy subjects demonstrated nonlinear kinetics of both the total and unbound drug in opposite directions, i.e., dose exposure related increase in the clearance of total drug and decrease in the clearance of the unbound drug. Decreased clearance of the unbound drug was related predominantly to a decrease in the volume of distribution and not an increase in the half-life. This phenomenon is considered to have minimal impact on drug accumulation upon multiple dosing. The apparent volume of distribution (Vd/F) of total oxaprozin is approximately 11-17 L/70 kg. Oxaprozin is 99% bound to plasma proteins, primarily to albumin. At therapeutic drug concentrations, the plasma protein binding of oxaprozin is saturable, resulting in a higher proportion of the free drug as the total drug concentration is increased. With increases in single doses or following repetitive once-daily dosing, the apparent volume of distribution and clearance of total drug increased, while that of unbound drug decreased due to the effects of nonlinear protein binding. Oxaprozin penetrates into synovial tissues of rheumatoid arthritis patients with oxaprozin concentrations 2-fold and 3-fold greater than in plasma and synovial fluid, respectively. Oxaprozin is expected to be excreted in human milk based on its physical-chemical properties; however, the amount of oxaprozin excreted in breast milk has not been evaluated.

    Prescribing Information for Daypro (Oxaprozin); G.D. Searle LLC, Div. of Pfizer Inc, USA; (January 2007). Available from, as of February 12, 2008: https://media.pfizer.com/files/products/uspi_daypro.pdf

    Daypro is 95% absorbed after oral administration. Food may reduce the rate of absorption of oxaprozin, but the extent of absorption is unchanged. Antacids do not significantly affect the extent and rate of Daypro absorption.

    Prescribing Information for Daypro (Oxaprozin); G.D. Searle LLC, Div. of Pfizer Inc, USA; (January 2007). Available from, as of February 12, 2008: https://media.pfizer.com/files/products/uspi_daypro.pdf

    It is not known whether oxaprozin is distributed into human breast milk. However, it is distributed into the milk of lactating rats.

    Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 382

    Approximately 5% of the oxaprozin dose is excreted unchanged in the urine. Sixty-five percent (65%) of the dose is excreted in the urine and 35% in the feces as metabolite. Biliary excretion of unchanged oxaprozin is a minor pathway, and enterohepatic recycling of oxaprozin is insignificant. Upon chronic dosing the accumulation half-life is approximately 22 hours. The elimination half-life is approximately twice the accumulation half-life due to increased binding and decreased clearance at lower concentrations.

    Prescribing Information for Daypro (Oxaprozin); G.D. Searle LLC, Div. of Pfizer Inc, USA; (January 2007). Available from, as of February 12, 2008: https://media.pfizer.com/files/products/uspi_daypro.pdf

    For more Absorption, Distribution and Excretion (Complete) data for OXAPROZIN (8 total), please visit the HSDB record page.

    5.6 Metabolism/Metabolites

    Hepatic. Ester and ether glucuronide are the major conjugated metabolites of oxaprozin, and do not have significant pharmacologic activity.

    Several oxaprozin metabolites have been identified in human urine or feces. Oxaprozin is primarily metabolized by the liver, by both microsomal oxidation (65%) and glucuronic acid conjugation (35%). Ester and ether glucuronide are the major conjugated metabolites of oxaprozin. On chronic dosing, metabolites do not accumulate in the plasma of patients with normal renal function. Concentrations of the metabolites in plasma are very low. Oxaprozin's metabolites do not have significant pharmacologic activity. The major ester and ether glucuronide conjugated metabolites have been evaluated along with oxaprozin in receptor binding studies and in vivo animal models and have demonstrated no activity. A small amount (<5%) of active phenolic metabolites are produced, but the contribution to overall activity is limited.

    Prescribing Information for Daypro (Oxaprozin); G.D. Searle LLC, Div. of Pfizer Inc, USA; (January 2007). Available from, as of February 12, 2008: https://media.pfizer.com/files/products/uspi_daypro.pdf

    5.7 Biological Half-Life

    54.9 hours

    Upon chronic dosing the accumulation half-life is approximately 22 hours. The elimination half-life is approximately twice the accumulation half-life due to increased binding and decreased clearance at lower concentrations.

    Prescribing Information for Daypro (Oxaprozin); G.D. Searle LLC, Div. of Pfizer Inc, USA; (January 2007). Available from, as of February 12, 2008: https://media.pfizer.com/files/products/uspi_daypro.pdf

    5.8 Mechanism of Action

    Anti-inflammatory effects of Oxaprozin are believed to be due to inhibition of cylooxygenase in platelets which leads to the blockage of prostaglandin synthesis. Antipyretic effects may be due to action on the hypothalamus, resulting in an increased peripheral blood flow, vasodilation, and subsequent heat dissipation. Oxaprozin is a non-selective NSAID, with a cell assay system showing lower COX-2 selectivity implying higher COX-1 selectivity.

    This study was undertaken to evaluate the scavenging activity for reactive oxygen species (ROS) and reactive nitrogen species (RNS) by several nonsteroidal anti-inflammatory drugs (NSAIDs), namely indole derivatives (indomethacin, acemetacin, etodolac), pyrrole derivatives (tolmetin and ketorolac), and an oxazole derivative (oxaprozin). The inhibition of prostaglandin synthesis constitutes the primary mechanism of the anti-inflammatory action of these drugs. Nevertheless, it has been suggested that the anti-inflammatory activity of NSAIDs may be also partly due to their ability to scavenge ROS and RNS and to inhibit the respiratory burst of neutrophils triggered by various activator agents. Thus, the scavenging activity of these NSAIDs was evaluated against an array of ROS (O(2)(-), HO, HOCl, and ROO) and RNS (NO and ONOO(-)) using noncellular in vitro systems. The results obtained demonstrated that tolmetin, ketorolac, and oxaprozin were not active against O(2)(-), while acemetacin, indomethacin, and etodolac exhibited concentration-dependent effects. Oxaprozin was also the least active scavenger for HO, among all the tested NSAIDs shown to be active. The scavenging effect for HOCl was not observed for any of the tested NSAIDs. The ROO was effectively scavenged by etodolac, with the other tested NSAIDs being much less active. NO and ONOO(-) were scavenged by all the tested NSAIDs.

    PMID:15528048 Fernandes E et al; Free Radic Biol Med 37 (11): 1895-905 (2004)

    Oxaprozin is a nonsteroidal anti-inflammatory drug characterised by a propionic acid-based structure. It is able to diffuse easily into inflamed synovial tissues after oral administration. Although discovered > 20 years ago, it is now under intensive investigation because of its unusual pharmacodynamic properties. Other than being a nonselective cyclooxygenase inhibitor, the drug is capable of inhibiting both anandamide hydrolase in neurons (median inhibitory concentration [IC50] = 85 umol/L), with consequent potent analgesic activity, and NF-kappaB activation in inflammatory cells (IC50 = 50 umol/L). Moreover, oxaprozin induces apoptosis of activated monocytes in a dose-dependent manner, with the effect being detectable at a concentration of 5 micromol/L and reaching the maximum activity at 50 umol/L. As monocyte-macrophages and NF-kappaB pathways are crucial for synthesis of proinflammatory and histotoxic mediators in inflamed joints, oxaprozin appears to be endowed with pharmacodynamic properties exceeding those presently assumed as markers of classical nonsteroidal anti-inflammatory drug.

    PMID:15934904 Dallegri F et al; Expert Opin Pharmacother 6 (5): 777-85 (2005)

    API Reference Price

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